Oh god where to begin... I have a few goodies.
I play a lot of Country gigs. I don't change how I dress or anything for the vast majority (unless it's a nice place) of events. I'll wear my battle jacket complete with band patches a la Motley Crue, Iron Maiden, White Zombie, etc. The band requested I do this because when I auditioned they were wanting a rock bass player to fill in the dead space on some of the more simplistic songs. I obliged. Well we were playing a pretty good sized gig at a bar in a small town in Kentucky. Right before we come back from break we were waiting on a guest singer to come up and I start playing a few bars of Stranglehold, NIB, and a few other little bits. The band join in just to fill some space. After the show some big burly looking biker dudes walk over to me and offer to buy me beer and insist that "The band should turn me loose next show and we need to either play some Megadeth or some Black Sabbath" because "That s*** is better than some of the country stuff". Was funny as can be, and wasn't so much of an offer as it was a "What the hell?" moment.
The weirdest offers I have had are two tossups: One of them being with my punk band. Our lead guitarist is the bass player in a rather big band, so I catch a lot of facebook ads from his fans which is fine. But we had one dude who wanted to book us in some part of Texas (We are based out of Kentucky, our lead guitarist is in Virginia), pay our gas, pay for the show, but have us sleep at his house and have his wife cook for us.
The other weird one was probably the time some 65 year old lady walked up to me and basically propositioned me for a bathroom fun time session. I just kind of went "uh.... What?". That was followed by the most awkward attempt at a sexual flourish pose I have ever seen and a "Don't be afraid just because I am older and more experienced". I laughed maniacally and walked away. I felt bad for that reaction, but I just could not contain it. I was about 25 at the time. She picked up some 18 year old later that night if I recall. Good on her, I suppose.